And how do you know when it is enough? I just read mystery's book and I feel like this is where I go wrong, thats why my game is so unpredictable, i generally can pick up, its just so random which ones, generally they are drunk or tipsy...

Build up your value then show an insecurity, that works great.

First off, the nature of the game is always going to be unpredictable. There's nothing you can do about that. You can be an hour in-set with an amazing HB9 and then her ex can stumble into the club and steal her right out of your arms. One day you get the worst reactions from sets of 6s and 7s, the next a 10 opens you. That's life! And yes, if you're doing night game in clubs, chances are the girls will be drunk, duh.

Anyway, how do you know your sticking point is comfort? What exactly is the wall you keep running into during your sets? Are girls calling you a player, refusing to come home with you, or asking "why do you like me" and putting up tons of LMR when you do get them home?

First off, qualification is the point at which you start screening for characteristics and getting them to tell you about themselves. For example, if you're looking for the SNL, then telling a story about your friend Anne who is so much fun to hang out with because she's so spontaneous and wild and will always make your night fun because you never know if she's gonna jump up on the bar or have an impromptu swim in a fountain or headbutt the bouncer, is a good way to start. Then when she starts telling you wild stories about herself, you compliment her about it.

A good way to get comfort going is to give away a little "embarrassing" detail about yourself. Actually, the embarrassing story can be a DHV story. For example "you know, I don't usually tell most people this, but I actually used to be in an acappella group in college. Yeah some people say it's lame but it was actually really fun, we would always be travelling to other colleges to perform, have groups host us and have crazy parties, like this one time...." etc. Then she gives you some embarrassing fact about herself, you listen and ask pertinent questions at the right times, qualify her, and then she feels a real connection with you.

Then you fuck the shit out of her.

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Simple idea for you to wrap your mind around, because if you were able to wrap it around a whole book, this should easily etch itself in your brain.
Opposites attract
Just show her an insecurity, and you should have her security.

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Everything I'm not made me everything I am/

you also might be focusing/working at comfort way too early.. you didn't really clarify when you were trying to build comfort and from the sounds of it it sounds like you're trying to incorporate it way early. comfort always comes later.. at first you should be working on rapport and attraction, once those are mastered then you can start giving her a reason to trust/feel comfortable with you (trust = comfort)

also, comfort is definitely something to be eased into, not an instant flip of a switch type thing. it CAN happen quickly, and actually it usually does if you're really vibing with a girl as you should be (in terms of, for example, your first day2 together), but it should never be forced or rushed. just be a genuine guy, let her see your legitimacy. it should come naturally. if it doesn't, you need to build more rapport and attraction.

rapport + attraction = comfort

oh, and, to re-quote blondguy.. yeah, once that comfort is there, you'll KNOW. you won't have to question it, it'll feel right. then proceed with the shit-fucking.